Southwest Announces Hawaii Flights: What You Need to Know Now

What used to be the country’s scrappiest and quirkiest little airline is now ready to play with the big boys. Late last night, Southwest Airlines officially announced plans to fly to Hawaii. Can you feel the Aloha LUV?

Southwest’s plans for Hawaii service have been the subject of many rumors the last few months. With a big focus on California travel, it only makes sense that the airline would eventually fly to one of the most popular leisure travel destinations for California residents. Getting the logistics and certifications in place, however, always takes time.

If you are a regular reader, you know how much I adore Southwest airlines for family travel. With no checked bag fees, no change fees, early boarding for families (between Groups A & B), and a courteous and kind staff, flying Southwest with kids in tow is a much more pleasant experience than with other US airlines. It probably goes without saying that I am psyched about this addition to the Southwest route map for families.

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Where and When is Southwest Flying to Hawaii?

Sunset on the Big Island of Hawaii.

Although many air travel gurus had been expecting a big announcement with dates and routes, unfortunately details at this points on both timing and destinations are scant. All we know so far is that the airline will begin selling tickets some time in 2018 “subject to government approval.” We don’t know when flights will start after that, although I’d expect several months at least between tickets going on sale and the routes actually starting to fly. Often that gap is 6 months or more, judging by other destinations Southwest has added in recent years (like its Caribbean and Mexico routes). So best case scenario seems like second half of 2018. More realistically, it could be as late as 2019.

As for destinations, we don’t know that yet either. Speculation is rampant, but I think it is safe to say that several California airports will be the focus. Southwest CEO Gary Kelly made reference to California in yesterday’s press release. I’d put my money on several of these airports if I were a betting gal: Oakland (OAK), San Diego (SAN), Los Angeles (LAX), and San Jose (SJC). Of course, with Oakland airport just a 12 minute drive my house, that just might be wishful thinking on my part.

And as to where Southwest will fly in Hawaii, I think it’s probably safe to assume HNL will be covered at first for sure. No word on whether other major Hawaiian airports like Kona on the Big Island (KOA), Maui (OGG), and Kauai (LIH) are initial or later stage contenders.

The airline will be flying the new 737-MAX on these routes (although it plans to start flying the 737-800 temporarily).

What’s Next for Travelers Wanting to Fly Southwest to Hawaii

So what should family travelers looking to get into the Aloha spirit know and be doing to prepare to take advantage of these new routes? Here’s my advice (with a little speculation thrown in for good measure).

Look Out for Fare Wars

More competition is almost always good for the consumer. I’m hopeful that the addition of more competition to Hawaii will drive already pretty competitive fares downward a bit more. Looking at my home market of Oakland, both Alaska and Hawaiian have pretty extensive service that is usually priced fairly reasonably. With three airlines in the mix, I’m going to be hunting for deals if Southwest positions any of these flights at OAK.

Time to Snag Southwest Credit Cards

So you wanna go to Hawaii on the cheap? Of course you do. If you already have a stash of Rapid Rewards points, save them up to redeem for award travel for sure on these new routes.

If you don’t have a bank of Rapid Reward points, start building one up! One of the easiest ways to earn Rapid Rewards flights that you can redeem for free travel on Southwest is through the co-branded credit cards from Chase. My family regularly has one or two of them in our wallets. The current signup bonus for both of the personal cards as of October 12, 2017 is 40,000 points for spending $2000 within three months (annual fee not waived).

Remember also that Chase Ultimate Rewards points transfer 1:1 to Southwest Rapid Rewards points. So if you have one of the Chase cards that earns these valuable rewards, then you are all set too. My family currently has both the Chase Sapphire Preferred and Chase Sapphire Reserve cards as well as the Chase Freedom card (which doesn’t earn the same transferrable points when held by itself but can when paired with one of the premium cards).

Southwest Companion Pass Prep

If you are a veteran of the miles and points world, I’m sure you know all about the Southwest Companion Pass. If you are a regular person, that term probably means little.

The bottom line: the companion pass is a pass that allows a flyer to take a single companion with them on any Southwest flight totally free (plus taxes and fees). As you can probably imagine, it’s pretty valuable for saving money for couples and families who fly Southwest often. It might be even more valuable on these more expensive Hawaii routes. Many folks are rushing to earn one ASAP.

You have to early 110,000 Rapid Rewards points in a single year to get a Companion Pass. Many people earn it by good old fashioned “butt-in-seat” flying. But it’s possible to do with a combination of several credit card bonuses as the miles and points world does. My word of warning – this method is not exactly for the beginner even though there are blogs that make it sound like a piece of cake. Believe it or not – I’ve never had a companion pass myself (shocker!). If you are ready to do some research and legwork, now certainly seems to be the time though.

A lot of ink has been spilled on the Southwest Companion Pass so I’ll spare you more. Here are a few of the more comprehensive guides out there if you think it might be for you and want to learn how to do it.

There are many gurus who are predicting the addition of Hawaii to the Southwest route map may result in fundamental changes to the companion pass. That is probably true long term, but I think the companion pass as we know it is a safe bet for 2018 and probably also 2019 too.

Are you excited about Southwest flights to Hawaii? Share your thoughts and plans in the comments.

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I actually thought getting the companion pass the first time around for SW was a piece of cake and not complicated at all. I’ve had one for the past three years and one of the best “investments” I ever made.

Great to hear! I tried to do it once with a combination of a personal + a business credit card but could not get approved for the business card no matter what I did. That hack is not as easy as it used to be unless you have credit history (preferably with Chase) for the business.

About

Welcome! I’m Leslie, a mom of two (ages 8 and 3) who loves to travel. Trips With Tykes is a family travel blog devoted to simplifying the logistics of traveling with young kids. With a little knowledge of airline rules & good planning, family travel can be really fun, even if it still involves the occasional in-flight tantrum or battle with TSA over your toddler’s juice box.